5. Paul Merson
One of the best players to grace the Premier League during the 1990's, Paul Merson became one of Arsenal's greatest legends and also has an excellent reputation for his time at Aston Villa. Like the person next on this list, he too was plagued by alcohol problems which deprived him of reaching greater heights. In 2003 he joined Championship side Walsall as he entered the final act of his career and was thrust into the managerial position after the sacking of Colin Lee. He got Walsall relegated and was shockingly given a contract extension and the job permanently. Walsall barely survived consecutive relegations after a late season resurgence and it was clear Merson was incredibly out of his depth but he was given to live to fight for another season. Merson's only managerial job to date ended after a 5-0 thrashing to Brentford and he can now be seen spouting nonsense on Gilette Soccer Saturday and showing no signs of coming out of managerial exile.